As conventional processes for preparing an optically active biaryl compound, for example, cross-coupling of N-(t-butyloxycarbonyl)-O-(trifluoromethanesulfonyl)-tyrosine methyl ester which is a derivative of a natural amino acid tyrosine, with phenylboronic acid in the presence of a palladium catalyst (WO 2001-36376); cross-coupling of N-FMOC-4-(trimethylstannyl)phenylalanine t-butyl ester with a halobenzene in the presence of a palladium catalyst (WO 2001-12183); cross-coupling of N-(t-butyloxycarbonyl)-4-iodophenylalanine methyl ester with phenylboronic acid in the presence of a palladium catalyst (WO 2000-43372), etc. are known.
However, the above-mentioned cross-coupling methods have problems in the process. For example, a problem is that these methods use expensive palladium catalysts and therefore the catalysts are required to be collected after the reaction. Furthermore, syntheses of reaction substrates are complicated because the leaving groups of the reaction substrates, aromatic compounds are a trifluoromethanesulfonyloxy group, which is synthesized using expensive and high caustic trifluoromethanesulfonic anhydride; a halogen, which has problematic position selectivity for introduction onto an aromatic ring; a trimethylstannyl group, which is derived from the halogen, and the like. Therefore, these methods are not necessarily satisfactory in industry.